Loneliness is something that has followed me throughout my life and it's something that I've simply learned to live with. Even at school I was isolated and seen as 'different' because I had a natural curiosity about life and wanted to do well so homework was always done on time and done to the best of my ability. I was top of the class in most subjects with an IQ of 156 and I soon discovered that boys just didn't like this sort of ability in a girl. They seemed very immature to me and I reasoned that a relationship would only be possible for me once they had grown up enough to appreciate me as an intelligent and independent woman.
Obviously it turned out grown men aren't naturally drawn towards these qualities either! It might have been different if I was 'hot' but I was aptly named Jayne Evans by my parents as I was every inch a 'plain Jane'. It's not that I've ever been ugly, fat or anything like that but I've equally never had any feature that would make me stand out to men. I'm a size 14 so I don't stand out as particularly big but I could stand to lose a few pounds and it certainly means I don't have the slim figure that men seem to love. My breasts are a good size at 38E and have stayed reasonably firm for a woman now in her late fifties but my overall size meant that they have never particularly stood out to a man. I've never been particularly pretty and I've always been so focused on my work and my career that I've never really bothered much with make-up, hairstyles or clothes. The overall result is that I tend to blend into the background and I think that's the worst fate of all for a 'plain Jane' like me because life can be very boring without ever being obviously bad.
I worked as an accountant for a top firm in London and I earned a very good living, allowing me to retire a few years ago but I'd never risen to the heights my intelligence and ability warranted because those in charge were men and they either promote their own or they promote the beautiful women who would project the right image of the company. That wasn't me so having been passed over for promotion yet again, I eventually decided to call it a day and took early retirement. I could survive financially if I was prudent and turning my back on London, I moved to Norfolk where I lived on a luxurious wide-beamed narrowboat moored in a tranquil area of great natural beauty. Life was peaceful and pleasant but also quite lonely.
It was a sunny summer's morning in July and I was lying in bed wondering what I would do to fill my day. The gentle undulations of the boat on the river were relaxing and my thoughts drifted to how nice it would be to share this beautiful morning with a special man in my life; a man who would make me feel special instead of plain and want to make love to me instead of ignore me. Since my retirement, it's fair to say that I'd been thinking a lot more about men! I'd been on a few dates over the years but nothing had ever really come of them other than dinner and a few kisses so here I was, a lonely spinster who was embarrassingly still a virgin. My career had meant that I didn't really stop to think of men and sex too much but now that I was retired and on my own, I was acutely aware that time was running out. I didn't feel I needed to be married anymore as I'd grown accustomed to my independence but I did long for some intimate physical contact with a man, if only to see what it was like!
I closed my eyes and allowed my hands to wander from my breasts, down between my legs and imagined it was a lover who actually wanted me. The area between my legs tingled at the thought but it was difficult to imagine just what it would be like with no actual experience. I'd seen couples have sex on TV and in films before and I'd seen pictures of naked men that certainly aroused me but I was sure that reality would be very different. Sadly, all my vagina had ever known was my own fingers or a modestly sized vibrator that didn't honestly feel very life-like to me. As pleasant as it could be, I was sure a man would feel a lot better. Unfortunately, at my age that was never likely to happen.
Eventually dragging myself out of bed, I decided to go for a walk along the river. I'd gone about half a mile when I passed another narrowboat moored to the riverbank. I'd seen it quite a few times before and chatted casually to the owner, who was a friendly guy called Scott. I never had a strong sense of any attraction to me but I'd never really sensed that from any man. Nevertheless, we did seem to get on well and the conversation was always warm and easy. He was in his mid-forties and quite a good looking guy without being in any way spectacular. Like me he carried a few extra pounds, as you might expect in middle-age but generally speaking he had a good body that looked firm and muscular. He'd been married but lost his wife a few years ago in a car accident and had been living on this narrowboat ever since.
I decided to go over and say good morning if he was around, though there was no sign of activity on board. The curtains appeared to still be closed so it seemed he was having a lie in but just as I was about to give up and move on, I noticed a gap in the curtains. I should have just passed by but who doesn't take a quick peek out of curiosity in such a moment? Scott was lying in bed with his eyes closed and the covers only up as far as his navel, exposing his firm and slightly hairy chest. As nice as that was for a frustrated older woman like me, what really attracted my attention was the fact that judging by the movement of the bedclothes, he was masturbating and getting close to orgasm.
Everything told me to hurry away before I was spotted but I was transfixed by what I was seeing and I hoped that at some point he would remove the covers altogether so I might see his erection. With such a barren sex life, I longed to just see a man's erection in the flesh. Unfortunately that didn't happen and I merely heard him moan as he climaxed into the sheets. It looked to be an intense experience for him and I was starting to breathe heavily myself as I imagined him cumming in me. The combination of the sheets and his movement made it difficult to determine much but my impression was that Scott was handling some decent equipment under those sheets and I wished it was at least my hand on his equipment instead of his.
Knowing he would probably be getting up now, I quickly sneaked away and returned to my own boat before I could be discovered. In one sense I was mortified by what I'd seen but I was also thrilled at seeing a man is such a state of arousal. It had never occurred to me that Scott would ever need to masturbate but now I thought about it, I'd never seen him with any sort of female company and he was certainly still young enough to have a normal male sex drive. That would be difficult to satisfy if he was never going out to meet women. This thought fired my imagination and I started to fantasize about Scott finding comfort with me. I knew it was unrealistic to expect a man in his mid-forties to be interested in me but then if it was really possible, it wouldn't be a fantasy.
I spent the rest of the morning in my own bed, using my hands and imagination to give me some sense of the pleasure I was sure Scott could give me. Closing my eyes I imagined the slightly rough texture of the stubble on his chin, his hands roaming over my body and his erection in my hand and finally in my desperate body. It was a lovely way to spend a relaxing day but ultimately it could never be entirely fulfilling.
Days passed and I kept coming back to my fantasy but I couldn't help concluding that it was nothing but a ridiculous dream. As it happened, fate was able to give me a prod in the right direction. It had been a few days since I saw Scott masturbating and I was sitting on top of my boat, enjoying the warm summer sun when I heard a boat approaching from behind. It was Scott and my immediate instinct was to get out of sight but it was too late.
'Hi Jayne, how are things?' he called cheerfully.
'Perfect with this weather, thanks' I replied as casually as I could muster. 'It's good to see you again.' I could feel myself blushing at my unfortunate phrasing but he didn't notice. 'Where are you going?
'I'm heading up to Cromer for a few days, just for a change of scene but I'll be back before long. I prefer the peace and quiet we have here.'
'Me too' I agreed, wanting to say more but unsure exactly what it was that I could say in a conversation that was nothing but small talk. Flirty small talk wasn't exactly my forte given my lack of experience with men.
'Why don't you come over when I return and I'll cook you dinner' he said cheerfully. 'As we live so close to each other and in such a remote area, it's about time we got to know each other better.'
His generous offer was a surprise and I had mixed feelings about the whole thing. He did seem like a nice guy and getting to know him better, especially given my little fantasy, wouldn't be the worst thing in the world but he was right that this was a remote area so how safe would I be with a relative stranger?
